Dyes of the anthraquinone acid wool dyestuff series



1000 parts of 4% brine containin`g`25 parts of 20?- B, hydrochloricacid. The cake is then washed with 1000 parts of 4% brine and dried.`The re.-

sulting color dyes Wool a bright, level violet shade from the usualacid' bath, which chi'omes to a dull, green shade.

Example 8 8.08 parts of broma-mine acid (100%), 6.72 parts of sodiumbicarbonate, 9.18 parts of 2:5- dimethylol-aniline,1 20 parts of water,and .12 part ofcopper sulfate.5I-I2O, are heated at 75 C. for 12 hourswith stirring. On cooling 12 parts of sodium chloride are added and the4solution is stirred until the dye is precipitated. It is then lteredand the cake is dissolved in 400 parts of hot water. parts of charcoalare added and the solution vis filtered to remove the small quantity ofinsoluble material. parts of salt are added and the solution is cooledto C. The crystals are ltered oi, Washed with 5% brine, then 21/% brine,then finally with 1% brine and dried. The resulting color dyesl Woollevel blue shades.

Example 9 45 parts of lamino-4-bromo-5-hydroxy-2-anthraquinone sulfonicacid copper salt, 19 parts of meta-amino-benzyl alcohol, 33.6 parts ofsodium bicarbonate and 607 parts of Water are boiled under redux forseveral hours. Dilute hydrochloric acid is added until the reaction isacid toi Congo red. The solution is filtered at 25 C. The cake is heatedwith 1000 parts of hot water and 25 parts of concentrated hydrochloricacid,

then ltered at 25 C. The cake is dissolved in 1000 parts of hot water,and sodium carbonate is added until the solution is slightly alkaline toBrilliant yellow indicator. Five parts of Darco are then added and thesolution is filtered from the insoluble material. 'l1/2% saltconcentration, cooled to 25 C. and filtered. The cake is washed with 5%brine and dried. The resultingA color dyes wool bright 4greenish-blueshades, becoming duller and greener on top-chroming.

Example 10 40.0 parts of bromamine acid 100%, 20.5 parts of2-methyl-5-methylol-aniline, 33.6 parts of sodium bicarbonate, 600 partsof water, and .5 part of copper sulfateHzO, are heated at 75 C. for 12hours under stirring. On cooling the color i's iiltered off and isolatedas in Example 2. The

resulting color dyes wool bright blue shades.

Example 11 4.04 parts of bromamine acid 100%, 2.03 parts of3-amino-phenyl-methyl-carbinol, 3.36 parts of sodium bicarbonate, 40parts of water, and .06 part of copper sulfate.5H2O, are heated at 75 C.for 12 hours under agitation. 'I'he resulting color is worked up as inthe above examples ysalting to 5% after clarification and Washing with3% brine. The color dyes wool bright, very level shades of blue,

The ltrate is salted to ltions to give maximum yields will vary and may'be determined by simple experimentation in each The reactions ofbromamine acid, its homologues and analogues, with amines are wellknown,and the variations of time, temperature and proportions of reactantsdepend largely on the variation in the reactivity of the amino compoundused. Temperatures from to 100 C. are used while the amounts of theairline may be varied from 1.2 to 4 moles. The time required .forcarrying out the reaction may vary from one hour to twelve hours. Themost suitable condi- CaSe..

While in the above examples the colors are isolated as the yalkali metalsalts, (for potassium chloride may be used in place of sodium chloride)they may also be obtained in the form of the free sulfonic acids by theusual methods, such as by the acidication of a solution of the alkalimetal salt.

Other anthraquinone sulfonic acids which' will condense with arylamines,such as the quinizarine-5-(or 6) sulfonic acids; 1methylaminof4bromo24anthraquinone sulfonic acid, etc., may be condensed with thearylamines which carry the methylol group to produce colorswith-improved dyeing properties, since theA dyes, as above illustrated,which contain the methylol group, (hydroxymethyl) not contain thatgreater value, par7 dye wool in more level shades sponding compoundswhich do group, and are therefore of ticularly for machine dyeingpurposes.

These compounds particularly those prepared from the p-amino-benzylalcohols also serve, as intermediates in the preparation of other` dyesof the type described in copending application` of D. X. Klein, SerialNo. 362,626, filed of evendate herewith, for they are readily condensedwith diarylamines in which one aryl group is of the benzene series andis Aunsubstituted in the paraposition. The compounds of this applicationare also intermediates suitable for the preparation of cellulose acetatedyes by elimination of the sulfonic acid group as more particularlydescribed in our copending application Ser. No. 362,625, led of evendate herewith. i

We claim:

1. Compounds of the class consisting of larylaminoanthraquinone sulfonicacids and theiralkan metal sans in which the aryi groupis a monocyclicaryl radical, which carries in the aryl group the radical -LcHoH lIz inwhich R represents a substituent of the group consisting of CH3 and I-I.v i

2. Compounds of the class consistingy of 1-amino4arylamino2-anthraquinone s ulfonic acids and their alkali metalsalts in Whichthe aryl group is a. monocyclic aryl radical, l.whichcarries in the aryl group the radical w 3'. Compounds of the classconsisting or 1'- amino-l-arylamino-2-anthraquinoneV ,1 sulfcnlc acidsand their alkali metal salts in -whichthe carries in the aryl group theradical CH2-OH. ani1no 2anthraquinone sulfonic acid and its 4. 1-amino-4- (3 -hydroxymethylanilnw -2- alkali metal salts.

anthraqunone sulfonic acid and its alkali metal salts. 5 ALEXANDER J.WUERTZ.

5. 1-amino-4-(3'hydroxymethyl-4'methoxy DAVID X. KLEIN. an1no2anthraqunone sulfonic acid. and its alkali metal salts.

